4-羧甲基-3-硝基苯甲酸乙酯 | 1023942-16-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-羧甲基-3-硝基苯甲酸乙酯
• 英文名称: 4-carboxymethyl-3-nitrobenzoic acid ethyl ester
• 英文别名: ethyl 4-(carboxylmethyl)-3-nitrobenzoate；Ethyl 4-(carboxymethyl)-3-nitrobenzoate；2-(4-ethoxycarbonyl-2-nitrophenyl)acetic acid
• CAS: 1023942-16-6
• 化学式: C₁₁H₁₁NO₆
• 分子量: 253.211
• InChiKey: RUSUPBJOVKMNII-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-羧甲基-3-硝基苯甲酸乙酯 在 palladium 10% on activated carbon 、 氢气 、 溶剂黄146 作用下， 20.0 ℃ 、344.75 kPa 条件下， 反应 1.0h， 以83%的产率得到2-吲哚酮-6-甲酸乙酯
  参考文献：
  名称：

  Design, Synthesis, and Evaluation of Indolinones as Triple Angiokinase Inhibitors and the Discovery of a Highly Specific 6-Methoxycarbonyl-Substituted Indolinone (BIBF 1120)

  摘要：

  Inhibition of tumor angiogenesis through blockade of the vascular endothelial growth factor (VEGF) signaling pathway is a new treatment modality in oncology. Preclinical findings suggest that blockade of additional pro-angiogenic kinases, such as Fibroblast and platelet-derived growth factor receptors (FGFR and PDGFR), may improve the efficacy of pharmacological cancer treatment. Indolinones substituted in position 6 were identified as selective inhibitors of VEGF-, PDGF-, and FGF-receptor kinases. In particular, 6-methoxycarbonyl-substituted indolinones showed a highly favorable selectivity profile. Optimization identified potent inhibitors of VEGF-related endothelial cell proliferation with additional efficacy on pericyctes and smooth muscle cells. In contrast, no direct inhibition of tumor cell proliferation was observed. Compounds 2 (BIBF 1000) and 3 (BIBF 1120) are orally available and display encouraging efficacy in in vivo tumor models while being well tolerated. The triple angiokinase inhibitor 3 is currently in phase III clinical trials for the treatment of nonsmall cell lung cancer.

  DOI：

  10.1021/jm900431g
• 作为产物：
  描述：

  2-(4-(乙氧基羰基)苯基)乙酸 在 硝酸铵 、 硫酸 作用下， 以91%的产率得到4-羧甲基-3-硝基苯甲酸乙酯
  参考文献：
  名称：

  Design, Synthesis, and Evaluation of Indolinones as Triple Angiokinase Inhibitors and the Discovery of a Highly Specific 6-Methoxycarbonyl-Substituted Indolinone (BIBF 1120)

  摘要：

  Inhibition of tumor angiogenesis through blockade of the vascular endothelial growth factor (VEGF) signaling pathway is a new treatment modality in oncology. Preclinical findings suggest that blockade of additional pro-angiogenic kinases, such as Fibroblast and platelet-derived growth factor receptors (FGFR and PDGFR), may improve the efficacy of pharmacological cancer treatment. Indolinones substituted in position 6 were identified as selective inhibitors of VEGF-, PDGF-, and FGF-receptor kinases. In particular, 6-methoxycarbonyl-substituted indolinones showed a highly favorable selectivity profile. Optimization identified potent inhibitors of VEGF-related endothelial cell proliferation with additional efficacy on pericyctes and smooth muscle cells. In contrast, no direct inhibition of tumor cell proliferation was observed. Compounds 2 (BIBF 1000) and 3 (BIBF 1120) are orally available and display encouraging efficacy in in vivo tumor models while being well tolerated. The triple angiokinase inhibitor 3 is currently in phase III clinical trials for the treatment of nonsmall cell lung cancer.

  DOI：

  10.1021/jm900431g

文献信息

• NOVEL OXINDOLE DERIVATIVE
  申请人：Shinobu Noriaki

  公开号：US20100076049A1

  公开（公告）日：2010-03-25

  A compound or a pharmaceutically acceptable salt thereof of the present invention is represented by the following general formula (I): [wherein, R 1 to R 8 may have a hydrogen atom, a halogen atom, a hydroxy group, a C1-C6 alkyl group, a C2-C8 alkenyl group, a C1-C6 alkylcarbonyl group or —COOR 9 (wherein R 9 represents a hydrogen atom, a C1-C6 alkyl group or a C2-C8 alkenyl group) as a substituent; and X represents a sulfur atom, an oxygen atom or NR 10 (wherein R 10 represents a hydrogen atom, a halogen atom, a hydroxy group, a C1-C6 alkyl group, a C2-C8 alkenyl group or a C1-C6 alkoxy group)].

  本发明的化合物或其药学上可接受的盐的通式（I）如下：[其中，R1至R8可能是氢原子、卤素原子、羟基、C1-C6烷基、C2-C8烯基、C1-C6烷基羰基或—COOR9（其中，R9表示氢原子、C1-C6烷基或C2-C8烯基）作为取代基；X表示硫原子、氧原子或NR10（其中，R10表示氢原子、卤素原子、羟基、C1-C6烷基、C2-C8烯基或C1-C6烷氧基）]。
• Oxindole derivative
  申请人：Theravalues Corporation

  公开号：US08053461B2

  公开（公告）日：2011-11-08

  A compound or a pharmaceutically acceptable salt thereof of the present invention is represented by the following general formula (I): [wherein, R1 to R8 may have a hydrogen atom, a halogen atom, a hydroxy group, a C1-C6 alkyl group, a C2-C8 alkenyl group, a C1-C6 alkylcarbonyl group or —COOR9 (wherein R9 represents a hydrogen atom, a C1-C6 alkyl group or a C2-C8 alkenyl group) as a substituent; and X represents a sulfur atom, an oxygen atom or NR10 (wherein R10 represents a hydrogen atom, a halogen atom, a hydroxy group, a C1-C6 alkyl group, a C2-C8 alkenyl group or a C1-C6 alkoxy group)].

  本发明的化合物或其药学上可接受的盐由以下通式（I）表示：[其中，R1至R8可以是氢原子、卤素原子、羟基、C1-C6烷基、C2-C8烯基、C1-C6烷基羰基或—COOR9（其中，R9表示氢原子、C1-C6烷基或C2-C8烯基）作为取代基；而X表示硫原子、氧原子或NR10（其中，R10表示氢原子、卤素原子、羟基、C1-C6烷基、C2-C8烯基或C1-C6烷氧基）]。
• NOVEL HYDROXYINDOLE DERIVATIVE
  申请人：Theravalues Corporation

  公开号：EP2130829A1

  公开（公告）日：2009-12-09

  A compound or a pharmaceutically acceptable salt thereof of the present invention is represented by the following general formula (I): [wherein, R1 to R8 may have a hydrogen atom, a halogen atom, a hydroxy group, a C1-C6 alkyl group, a C2-C8 alkenyl group, a C1-C6 alkylcarbonyl group or -COOR9 (wherein R9 represents a hydrogen atom, a C1-C6 alkyl group or a C2-C8 alkenyl group) as a substituent; and X represents a sulfur atom, an oxygen atom or NR10 (wherein R10 represents a hydrogen atom, a halogen atom, a hydroxy group, a C1-C6 alkyl group, a C2-C8 alkenyl group or a C1-C6 alkoxy group)].

  本发明的化合物或其药学上可接受的盐由以下通式 (I) 表示： [其中，R1 至 R8 可具有氢原子、卤素原子、羟基、C1-C6 烷基、C2-C8 烯基、C1-C6 烷基羰基或 -COOR9（其中 R9 代表氢原子、C1-C6 烷基或 C2-C8 烯基）作为取代基；X 代表硫原子、氧原子或 NR10（其中 R10 代表氢原子、卤素原子、羟基、C1-C6 烷基、C2-C8 烯基或 C1-C6 烷氧基）]。
• EP2130829
  申请人：——

  公开号：——

  公开（公告）日：——
• US8053461B2
  申请人：——

  公开号：US8053461B2

  公开（公告）日：2011-11-08